How Agents Go Wrong

Agents fail in funny and scary ways — booking the wrong flight, sending wrong emails, running up bills.

Most failures come from misunderstanding the goal — agents are great at following directions, bad at noticing when they are heading off course.

Three common failure modes

• Misinterpreting ambiguous instructions
• Continuing too long without checking in
• Using the wrong tool for a task

The big idea: Agents fail in ways that are funny in retrospect — but only if you caught them in time.

Practice this safely

Try this with a school, hobby, or family example where the stakes are low. Use the AI output as a draft you can question, not as the final answer.

1. 1Ask AI to explain ambiguity in plain language, then underline anything that sounds uncertain or too broad.
2. 2Give it one detail from "How Agents Go Wrong" and ask for two possible next steps plus one reason each step might be wrong.
3. 3Check overconfidence against a trusted source, teacher, adult, expert, or original document before you use it.